


Win a Date With Dean Winchester

by destieldrabblesdaily



Category: Supernatural
Genre: AU, M/M, Strangers to Lovers, celeb!dean
Language: English
Status: Completed
Published: 2015-10-01
Updated: 2015-10-01
Packaged: 2018-04-24 08:22:57
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,754
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4912255
Author URL: https://archiveofourown.org/users/destieldrabblesdaily/pseuds/destieldrabblesdaily
Summary: <blockquote class="userstuff">
              <p>When Castiel's best friend Charlie wins him a date with his favorite movie star, Dean Winchester, Castiel gets more out of it than he'd expected.</p>
            </blockquote>





	Win a Date With Dean Winchester

Castiel was ready to pass out when he opened the door to his apartment. Almost midnight; as much as he enjoyed being a teacher, the parent-teacher nights that came with it were downright exhausting. A little terrifying even, considering that Becky Rosen’s mother, who was a single parent, had been hitting on him for twenty minutes straight. Castiel shuddered at the memory.

“Ah, there he is! You survived all the hungry singles, huh? Good on you!”

Watching TV on the couch was Castiel’s roommate Charlie, who was apparently still awake, shooting him a smirk as she shoveled more popcorn into her mouth.

“Barely.” Castiel huffed as he shrugged out of his coat and put down his briefcase.

Charlie passed him the bowl of popcorn the second he fell down next to her on the couch, and Castiel grabbed a handful, more out of habit than anything else.

“So, what is it we’re watching?” Castiel asked, glancing at the screen.

“Zombies, dude! No one lives!” She cheerfully informed him.

Castiel shrugged as he chewed his popcorn, never particularly picky.

When a commercial break happened ten minutes later, he was tempted to go to bed and call it a night. He was about to get up and do just that, when Charlie made a noise that sounded suspiciously like a  _screech,_ repeatedly smacking Castiel’s arm while doing so.

“Oh my god!” She exclaimed, pointing at the television.

Castiel’s heart skipped a couple of beats when he saw what she meant.

Green letters flashed across the screen, along with a picture of a familiar face. A face that Castiel knew quite well, because that right there was his favorite actor. Moss green eyes, freckles, and a confident smirk tugging at kissable lips.

_‘Donate $10.00 and win a date with Dean Winchester!’_

A friendly voice in the background explained that by making a small donation to the charity that Dean had helped set up, you’d automatically be in the race to win a dream date with one of America’s most popular actors.

The commercial ended, and Castiel felt as if he’d lost his voice. Charlie, on the other hand, was talkative enough for the both of them.

“You  _have_  to do it, Cas! You’ve been drooling over the guy since you were eighteen, you could go on an actual date with your celebrity crush, that’s like a fairytale!” She urged, all but jumping up and down in her seat like an overexcited monkey.

At the mention of the word fairytale, Castiel felt his stomach sink.

Somehow, this sounded a little  _too good_  to be true. And when being honest,  _Dean_  sounded too good to be true as well. It was one thing to admire someone’s talent and looks from afar, it was a whole other thing to actually go on a date with them. To possibly be disappointed when confronted with the fact that the person you admired came from a completely different planet. Besides, Castiel knew for sure that he wouldn’t be able to handle the spotlights that came with a date like that, on the off chance that he’d actually be selected to begin with.

It was crazy, a long shot, and on top of that it was doomed to backfire. And so he rolled his eyes at Charlie, ruffling her hair and playfully brushing her off.

“I think I’ll pass.”

Charlie being Charlie, she bugged him about it for the rest of the week. Castiel being Castiel, he bravely didn’t budge.

~

It was a regular Friday at Lawrence High; an unexpected fire drill, many misbehaving students, and a headache blooming behind Castiel’s eyes by the time the last class of the day had finally ended. He tiredly rubbed his forehead as he stepped outside, eager to go home, but paused when he realized that the parking lot was drowning in absolute  _chaos._

Usually, by the time the teachers left the building, the parking lot was already half empty. Today however, there were people  _everywhere_. Aside from that sea of people, there were cameras flashing left and right. Whatever was happening, clearly no one had bothered to leave Castiel a memo.

Castiel squinted, not all that interested in whatever was going on anyway and calculating whether or not he’d be able to make it to his Prius and leave.

_“There he is!”_

A squeal echoed through the parking lot, and Castiel held his breath when a rather attractive woman with dark skin and long wavy hair ran up to him, pushing a microphone right under his nose. She was followed by several guys who were carrying cameras, and many students, all of them using their phones to take pictures. All of the flashes were blinding Castiel, only adding to his confusion. That was until the woman spoke.

“Castiel Novak! How does it feel, knowing that you’ll be going on a date with the one and only  _Dean Winchester_?”

Castiel opened his mouth only to close it again, stunned to silence. Of one thing he was absolutely sure. He was going to  _murder_  Charlie Bradbury.

~

“Come on, grumpy pants, don’t give me that look.” Charlie pouted as she helped Castiel into his suit jacket. “I did it for you. Besides, your sister was in on it too.”

From behind them, Anna sighed dramatically. “There she goes, throwing me under the bus. Some friend.”

Charlie laughed, but didn’t even bother to deny it.

Castiel turned around to scowl at his sister, but his nerves were making it impossible for him to do much of anything. Anna ignored his half-assed attempt at a glare anyway, instead helping him with his tie, while Charlie supposedly ‘artfully’ messed up his hair.

“Prince Charming should be here in ten minutes, so it’s time to put on a smile.” Charlie hinted.

Ten minutes. Castiel was starting to feel nauseous. Anna noticed, and she pulled a disapproving face.

“Try to relax, Castiel. Green is not a good color on you.” She not-so-helpfully advised.

Castiel groaned, hiding his face in both his hands. Would it be too late to make an escape? Or perhaps he should just lock the door of the apartment and pretend they weren’t home. Ah yes, as if Charlie and Anna would ever let him get away with that.

“You two are cruel, you are the ones who are supposed to support me!” He accused, now restlessly pacing around the living room.  

Before the two redheads had a chance to come up with a witty comeback, there was the sound of the doorbell ringing. One simple sound that relentlessly announced the end of Castiel’s life as it was. He swallowed thickly, staring at the door as if it was his worst enemy.

“Go!” Charlie hissed, pushing him in the right direction.

With heavy feet, Castiel followed that order, knowing that there was nowhere to run or hide. His hands were trembling when he opened the door, his heart racing as an unfairly good-looking Dean Winchester was revealed, all dressed up, green eyes shining, even more handsome in the flesh.

When Dean flashed him a smile and greeted him like they’d been lifelong friends, Castiel was certain that he was about to faint.

“Heya, Cas… Ready to have some fun?”

Castiel nodded shakily as Dean took his hand, flashing cameras surrounding them; several reporters were making sure to get footage of every second of their first meeting. He suspected that Dean’s kind behavior towards him so far had to be an act -Dean was an actor, after all- and felt deeply uncomfortable with everything that was currently happening, even though Dean was obviously making an effort in front of their audience.

But then Dean leaned closer to him, placing a hand on the small of Castiel’s back, subtly whispering into his ear, making sure that no one else could hear.

“Shit… I’m lucky, you’re  _gorgeous_.” The actor breathed, voice smooth like honey, warm breath ghosting against the shell of Castiel’s ear, making him shiver. “Don’t worry about a thing, you’re doing  _great_.”

Castiel was feeling a little better when Dean took his hand and intertwined their fingers, leading the way. Even with all the press, Dean only had eyes for Castiel as they made their way to the limo that was parked right in front of the building. Castiel prayed that Dean wouldn’t notice his sweaty palms.

Whereas before Castiel had feared that Dean wouldn’t be as good as he’d hoped, he was now beginning to worry that maybe the guy was much  _better_ than Castiel had anticipated.

~

Castiel’s fears were confirmed not much later. They were at one of the only five star restaurants in the area, enjoying their appetizers while chatting over an expensive bottle of wine. Even though Castiel felt ridiculously out of place there, Dean wasn’t the problem at all.

They’d soon found out that they had plenty of things in common; they both liked Vonnegut, both enjoyed the beach, watched a lot of the same TV shows, and both had a special bond with their younger sibling. Dean was friendly, chatty, and surprisingly down-to-earth. Castiel had been so worried that they’d have nothing to talk about, but it was quite the opposite.

As it was, they were exchanging childhood stories; Dean told Castiel about all of the stunts that his younger brother Sam had pulled, and Castiel could relate, having experienced all of these things with Anna.

Nonetheless, Castiel was nervously shifting in his seat, because there were simply too many curious eyes on them. There were the other guests at the restaurant who by now knew what was going on there, and of course the reporters who all wanted the story of the famous actor on a date with one of his fans…

Castiel anxiously bit his lip as yet another camera flashed.

Out of the blue, Dean was reaching across the table, holding out his hand to Castiel, palm up. Castiel hesitated, having a hard time believing that Dean meant what Castiel thought he meant, but then tentatively placed his hand in Dean’s.

Dean smiled ruefully, squeezing Castiel’s fingers. “You don’t like it, this is clearly not gonna work.”

 _This is clearly not gonna work_. Blood turning cold, Castiel couldn’t stop his face from visibly falling. Wonderful. He’d sabotaged his own dream date because he couldn’t keep it together in front of a few cameras. They hadn’t even made it to the main course yet, and Dean Winchester was already done with him.

“I’m sorry… It’s not you, it’s… it’s  _everything else_.” Castiel apologized, smiling sadly, letting go of Dean’s hand. “But I’m glad I had a chance to talk to you, if you don’t mind me saying, you’re everything I hoped you’d be.”

“What?” Dean frowned, looking positively bewildered. “Cas no, that’s not what I’m saying.”

The tables had turned, Castiel being the confused one this time. “I’m afraid I don’t understand, Dean.”

Dean let out a breathless laugh, shaking his head. “I didn’t mean that  _we’re_  not gonna work, I meant that  _this place_  isn’t gonna work.”

“Oh…” Castiel replied, staring at the actor, speechless.

“Yeah, oh.” Dean teased, rolling his eyes but smirking. “Give me five minutes to make a phone call, then meet me at the exit.”

When Dean got up from his chair and pulled out his phone, winking at Castiel before he left the room, all Castiel could utter was a belated “Okay.”

~

“Where are we going?” Castiel pried. “You aren’t kidnapping me, are you?” He jokingly added, so much more at ease now that it was just the two of them.

Dean laughed, sincere and carefree, his smile touching his eyes. “I might… You’re a real catch, can’t blame me for wanting to keep you, Cas.”

Butterflies went wild in Castiel’s stomach at Dean’s blatant flirtation, even though it probably was merely part of the game.

They were back in the backseat of the limo, and they’d been driving for a good fifteen minutes. Their eyes met, and for the third time that night, Dean offered his hand to Castiel. Castiel gladly took it, and Dean almost shyly rubbed his thumb against the back of Castiel’s hand for the remainder of the drive.

Not much later they arrived at a destination unknown to Castiel, and when the driver gestured for them to get out of the car, Castiel was rendered speechless once more. They’d stopped at what appeared to be the middle of nowhere. The full moon was reflected in a small lake nearby, a blanket spread out next to a small group of trees, a basket and a bottle of champagne waiting for them. There was a path of tiny lanterns leading them to it, lighting the way.

Castiel was still caught up in his surroundings when Dean whispered into his ear.

“ _Better,_  Cas?”

~

The second Dean took the lid off of the basket and pulled out two ordinary burgers, Castiel knew that he was lost. He’d promised himself to not fall for the unattainable movie star, but Dean was making it extremely difficult for Castiel to keep that promise.

“I present to you, our main course. Much better than all that fancy crap, huh?” Dean declared proudly, grinning as he handed Castiel the ugly orange plastic plate with a burger on it.

“This is… It’s  _perfect._ ” Castiel admitted, smiling as he took the offered food.

“Believe it or not, but it took me years to get used to the circus that is my life. I enjoy acting… The other stuff that comes with it? Not so much.” Dean confessed before taking a large bite of his burger, moaning appreciatively as he did.

So this was it; eating burgers and drinking champagne under the stars with Dean Winchester. No date that Castiel would go on from now on would ever compare. He was ruined for everyone else by an actor who was going on this date because it was part of his job. Castiel now recalled why he had told Charlie that they  _shouldn’t_  do it. Castiel stared at the sky as he took a sip of champagne, avoiding Dean’s gaze while reality was starting to sink in.

He got away with it, for about five minutes.

“Something on your mind, angel?”

Startled by Dean’s voice, Castiel put down his glass and turned to look at him, surprised at the endearment.

Dean scooted closer to Castiel on the blanket, until their sides were touching. “My eh… My brother Sammy is into mythology and the supernatural and all that nonsense… You’re named after Cassiel, angel of solitude and tears, right?”

“Yes…” Castiel nodded, face heating up at the feeling of Dean’s body pressed against his.

“That’s what I thought.” Dean mumbled, putting down his glass as well, then casually resting his head against Castiel’s shoulder as if he wanted to belong there.

Castiel figured that if Dean started it, he was allowed to return his affections without ending up with a restraining order. He rested his head on top of Dean’s, and he lost track of time as they quietly talked and counted stars together.

“Hey Cas?” Dean said after a while, muttering the words against Castiel’s jaw. “Please tell me that there’s no boyfriend or girlfriend waiting for you at home…”

“There isn’t.” Castiel replied too quickly, then hesitated. “But surely there must be someone waiting for you.”

Not looking anywhere but the sky, Castiel’s heart pounded in his chest as he waited for Dean’s answer. But then Dean chuckled against his skin, two arms suddenly sneaking around Castiel’s waist and pulling him even closer.

“Wouldn’t be here doing this if I wasn’t single, Cas. Wouldn’t take it that far, I’m not  _that_  good an actor.”

A weight fell off of Castiel’s shoulders as Dean somehow accidentally addressed all of Castiel’s worst fears at once. He dared to properly look Dean in the eyes for the first time in a while.

“Can I have another date soon? A real one? We can do things at your pace, you know… Keep it private, no cameras.” Dean requested, looking up at Castiel with hopeful eyes.

That was an easy question. Castiel answered it by lightly nudging his nose against Dean’s, letting Dean know what he wanted, but also letting Dean decide. Dean laughed softly, getting the hint, gladly leading Castiel into their first kiss.

What Castiel  _didn’t_  know yet was that many more dates and kisses would follow, and that one year from now they’d be back at this exact same spot, where Dean would propose to him.

**Author's Note:**

> For more Destiel stories, go to destieldrabblesdaily.tumblr.com


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